An all-inclusive adventure (Part one: picking a destination)

For those of us nestled in the heart of the deep cold “American” north, a Caribbean “resort” vacation has a few notorious connotations: sun, beach, buffets, cringe-y awkward poolside group activities, along with infinite umbrella-wearing cocktails to leave you in a semi-permanent state of tipsy. And whether the idea of a pre-packaged all-inclusive relax-by-the-beach vacation is enticing or repulsive to you, it is hard to deny its illustrious simplicity– especially for the overworked vacationer on a budget.

As someone who typically falls into the “repulsed” (or at least apathetic) camp with these types of vacations, I had a hard time accepting this as the “best” option for my next adventure.

So how did I end up booking an all-inclusive resort made for kitschy destination weddings and quintessential honeymooners?

This brings me to one of the most important part of a planning a trip: picking a destination. 

When I hear about people’s trip planning woes, two sentiments typically stand out:

1) being afraid of the unknown or unconventional; and
2) feeling overwhelmed by the large amount of possibilities

In this two-part post I will use my upcoming trip to Jamaica to outline how to have an awesome, all-inclusive adventure with limited cost and hassle. In this first part I will breakdown the process of picking your destination in a way that allows you to step out of your comfort zone and try something new without losing the appeal of a relaxing getaway.

A relaxing getaway

Source: Blue Hole waterfalls and swimming hole by Nick Sherman is licensed under CC BY2.0 /modified

Imagine a game of “choose your adventure” based two main aspects: price and accommodation. But before you get started you have to identify your constraints.

Step one: Constraints
Although I can confidently say I take every opportunity I can to travel, a lot of people confuse this with an unrestrained approach to vacation. This couldn’t be further from the truth. So few of us can actually say we have no obligations or responsibilities that constrain our wants and desires. These constraints may be widespread (time and money) others may be specific to our own personal circumstances (family, health). Regardless, knowing and operating within these constraints actually makes more possible. If you plan diligently and responsibly you can save time and money and maximize the value and quality of your experience. It also means you save resources for other things – like more travel!

These are the constraints I faced when planning my upcoming trip:

  • Time: One week (which also meant I was keen to keep flight times to under 5 hours, if possible)
  • Budget: $1500 total (including everything, absolutely all of it).
  • Dates: had to be in the last week of June as this is a quieter time at work.

Step two: Price
This is where the fun begins. Start with flights from Toronto (or whatever airport is closest to your wanderlusting self) to Anywhere. You may have a varying budget, and varying travel times, but the key is to find a deal. Whether you are a seasoned traveller or exploring the world for the very first time it is important to accept the reality that the cost of your trip will reflect a bunch of variables. Date, season, weather, demand, oh the list goes on. This means that sometimes one destination will just not make sense, but another may entirely surprise you. This may be hard if you had your heart set on somewhere, but that’s why I would advise to keep your mind open. You may have your most memorable experiences in the most unlikely places.  So factoring in your own constraints (see mine above) and picking a destination based on the lowest price is key.

As you may know, when it comes to travel, I have some ambitious goals. Namely to visit 100 countries. Obviously this means I have to pick new> comfortable and unfamiliar> well-known. This means I am highly unlikely to be picking a place I have already been too (with a few notable exceptions). With this in mind Barbados, Bahamas, Bermuda, and Jamaica all made it to the short-list based on constraints and price.

Step three: Accommodation
Of course picking a destination is not just about price. But price should give you a short-list of places to “investigate” further. Since flights and accommodations will generally be the major cost (unless you are doing an activity-centric vacay, but that is a different discussion for a different post), having a clear idea of some accommodation options for your short-list of destinations is necessary to accurately cost out your trip. This step is about picking something that goes beyond your basic constraints and begins to address your preferences and desires.

Flight time, types of available accommodation, their price, and their amenities all play a role. Like I said, mine is a one-week trip with a budget. Thus, accommodation options were limited to airbnb and hostels. Unless of course… hmmm… you guessed it … unless I went for a pre-packaged deal with a flight and hotel included. But, at first I thought this wasn’t really what I wanted for my trip.

So why did I snub the airbnb and hostel options this time? First of all, availability was limited. Second, what was available seemed a little bit out-of-the-way. Which would mean that a rental car would be required (read: hassle, stress, and cost). In a moment of frustration, we clicked crucial (and dangerous) button: PACKAGES.

Here the doors of possibility flooded open – so many options! At the same time, because of their high price Barbados, Bermuda, and Bahamas all ceased to be options (maybe one day?). And while the options were plentiful they were limited to locations I had already been to (Domincan, Cuba, Mexico). Then there was Jamaica.

Jamaica just fit. So we booked our trip with Air Canada Vacations (bonus: aeroplan points!) at the Grand Bahia Principe in Runaway Bay, Jamaica. And the rest is history….

Well, actually it isn’t: if you want to learn how to turn your dull resort-bound vacation into an adventure check out my next post to find out how I am going to do just that!

One thought on “An all-inclusive adventure (Part one: picking a destination)

  1. Sigh… why, oh why, does it seem everyone is vacationing except for me?!! I can’t wait to hear how the trip goes! I haven’t done an all-inclusive in years, so I’m curious to know if they’ve still “worth it”!

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